Enter your name and email to receive alerts when new vacation deals are added to any property in this region.
By clicking "Submit" you are agreeing to the
Terms of Service.
Alert successfully created!
Showing 1-11 of 11 Resorts and Lodges
Convenient and comfortable, stay at the Holiday Inn Express Hotel and Suites in Chestertown, Maryland. Jump into the indoor pool or take a step into historic Chestertown; whether you sail on the Schooner Sultana, a working schooner ship nearby, or stop by the Chestertown Farmers’ Market or Artisans’ Market, the Holiday Inn is within easy... more
For over 100 years, The Imperial Hotel has stood in the historic district of Chestertown, Maryland. It offers comfortable accommodations in eleven deluxe rooms and two suites, all within walking distance of the best attractions in Chestertown. Take a walk through town for shopping, sightseeing, and Chestertown’s Washington College. Enjoy on-site... more
Rest and relax at this 28-room Inn, conveniently located in peaceful Chestertown. Lounge on your spacious colonial-style bed or splash in the outdoor pool. Some rooms even feature a jacuzzi style tub! And Driftwood Inn is within easy distance of all... more
Stay at Comfort Suites and experience the eastern shore of Maryland! Start your day with a free hot breakfast, then take a dip in the hot tub or splash in the pool. Venture out into Chestertown and enjoy nearby attractions like the Eastern Neck National Wildlife Refuge, Betterton Beach, and the Waterman's Museum. At the end of the day, return to... more
With only two rooms in this quiet and comfortable guest house, you’ll feel right at home at Simply Bed and Bread. Sit on one of the inviting wicker chairs on the porch and look over Chestertown, Maryland. Inside, delicious treats like fresh... more
The White Swan Tavern, a quiet, elegant home embedded in the history of Maryland's Eastern Shore, is for those who treasure serene streets, birdsong mornings, impeccable service and the grace of New World Tradition. The White Swan tavern has been restored to its 1793 appearance but its fascinating history predates 1733.... more
Built in 1938 as a private residence for Russell D’Oenche, the Georgian-style Great Oak Manor is an experience in elegance you won’t soon forget! Unwind in one of 12 gracious period-themed guest rooms featuring private baths, balconies with Chesapeake Bay views, and replica antiques. And, make sure to roam the beautifully manicured lawns, enjoy... more
Five beautifully furnished rooms, each with its own private bath, await you at Lauretum Inn Bed and Breakfast. Savor a delicious continental breakfast, then take one of the inn's bikes for a spin. And, as a guest to Lauretum Inn, you are entitled to... more
Finished in 1860 as the plantation house of the areas largest peach grower; Brampton retains today nearly all of its original details. They include the magnificent three and a half story central staircase, walnut windows and doors, original heart pine floors and plaster ceiling medallions. This thirty-five acre estate is conveniently located... more
Located in historic Chestertown on Maryland’s upper eastern shore, Widow’s Walk Inn provides comfortable lodging in its five rooms with the warm atmosphere of a family home. Whether you play a game or read a book in the parlor or relax... more
Put yourself in the midst of American history by staying at Mitchell House. Rest in one of the six comfortable rooms or, for added privacy, relax in the one-bedroom Stone’s Throw Cottage. This colonial house is just minutes away from Historic... more